WO2006128809A1 - Materiau destine a des couches electrochromes - Google Patents

Materiau destine a des couches electrochromes Download PDF

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Publication number
WO2006128809A1
WO2006128809A1 PCT/EP2006/062538 EP2006062538W WO2006128809A1 WO 2006128809 A1 WO2006128809 A1 WO 2006128809A1 EP 2006062538 W EP2006062538 W EP 2006062538W WO 2006128809 A1 WO2006128809 A1 WO 2006128809A1
Authority
WO
WIPO (PCT)
Prior art keywords
dye
component
redox
electrochromic
material according
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/EP2006/062538
Other languages
German (de)
English (en)
Inventor
Andreas Kanitz
Wolfgang Roth
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Siemens AG
Siemens Corp
Original Assignee
Siemens AG
Siemens Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Siemens AG, Siemens Corp filed Critical Siemens AG
Publication of WO2006128809A1 publication Critical patent/WO2006128809A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K9/00—Tenebrescent materials, i.e. materials for which the range of wavelengths for energy absorption is changed as a result of excitation by some form of energy
    • C09K9/02—Organic tenebrescent materials
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/15—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on an electrochromic effect
    • G02F1/1514—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on an electrochromic effect characterised by the electrochromic material, e.g. by the electrodeposited material
    • G02F1/1516—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on an electrochromic effect characterised by the electrochromic material, e.g. by the electrodeposited material comprising organic material
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/15—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on an electrochromic effect
    • G02F2001/1502—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on an electrochromic effect complementary cell
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/15—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on an electrochromic effect
    • G02F1/1514—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on an electrochromic effect characterised by the electrochromic material, e.g. by the electrodeposited material
    • G02F2001/15145—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on an electrochromic effect characterised by the electrochromic material, e.g. by the electrodeposited material the electrochromic layer comprises a mixture of anodic and cathodic compounds

Definitions

  • the invention relates to a material for electrochromic layers based on an activated by redox reaction color change.
  • Electrochromic displays based on organic materials normally comprise an active electrochromic layer, which in the case of a display is located between electrodes arranged perpendicular to one another.
  • Essential components of the active layer are a redox system and a pH-active dye.
  • a voltage By applying a voltage, the concentration ratio of the redox partners to one another in the material is shifted. In this reaction protons and / or ions are released or bound in the material, which has an effect on the pH.
  • a voltage is applied to the material, the shift in the equilibrium of the redox partners on the two electrodes is in the opposite direction. As a result, the pH of one of the electrodes rises while it sinks on the counter electrode. Via a pH dye, the change in the pH value is then converted into a color change of the material and the application of the voltage is made visible.
  • a pasty formulation which represents the electrochromic system, is located between the electrodes.
  • the composition of this electrochromic system comprises as essential components a polymer as a solid electrolyte, a conductive salt, a redox system, TiO 2 as a white pigment, a solvent and a dye. This is usually a pH indicator.
  • the drawback of this formulation is the redox system.
  • the redox system based on quinone / hydroquinone generates a pH environment at the electrodes, which in particular uses the ITO (indium-tin) used as the transparent electrode material. Oxide) in acidic as in the alkaline chemical attack. This electrode corrosion results in the impairment or loss of the electrode function. As a result, the function of the electrochromic cell and thus the life of the display is limited.
  • the object of the present invention is therefore to specify a material for an electrochromic formulation which on the one hand manages without a redox system based on hydroquinone / quinone and on the other hand has a not so limited coloration as the electrochromic formulations based on Viologens and / or polythiophenes.
  • the object of the invention and solution of the object is a material for an electrochromic formulation comprising at least one polymer as solid electrolyte, a conducting salt, a redox system, a white pigment, a solvent and a chromophore, the functionality of the redox system and of the Chromophors are connected in one component.
  • the component is an organic redox chromophore such as the merocyanine and / or polymethine dyes.
  • Organic redox chromophores used according to the invention are, in principle, all dyes of the so-called merocyanine and polymethine dye type.
  • a structural element in these dye types is basically quinoid in character. This chinoid structural element can be chemically as well as electrically (cathodic) reduce to the leuco form of the dye. In this process, the quinoid substructure is hydrogenated and converted into an aromatic compound that is conjugatively decoupled from the rest of the system. Conversely, one can chemically as well as electrically (anodically) recover the dye (the fully conjugated form) oxidatively.
  • Such chromophores used in an electrochromic arrangement are thus a redox couple and a coloring structure in one.
  • A is a donor substituent
  • B is an acceptor substituent which carries a positive charge in the case of a polymethine dye
  • R 1 and R 1 * are each independently H, alkyl (branched or unbranched Cl to ClO), aryl (preferably phenyl) or both are connected via an oxygen atom or sulfur atom,
  • R equal to Cl or substituted by an LN- (4-dimethylaminopyridine) radical; and in the event that the redox dye is a polymethine dye, an additional charge neutralization anion advantageously substituted betainically on the dye cation is necessary.
  • merocyanines derived from 1,3-diketones or from their cyclic ureides are of interest, such as the donor-substituted barbituric acid derivatives and thiobarbituric acid derivatives.
  • redox chromophores from the classes of merocyanines and methine dye betaines are known in principle, they are not the specific representatives of the respective chromophore classes that are suitable for use as electrochromes.
  • the known methine dye betaines usually lack the required te solubility and stability in specific solvents for the preparation of the formulations.
  • suitable for use redox chromophores from the above classes can not be easily prepared from the known and commercially available dyes, but can only be prepared from previously synthesized appropriately substituted synthons by condensation.
  • the following components are mixed in the amount indicated: TiC> 2 (Ig), polyethylene oxide (Ig), tetrabutylammonium tetrafluoroborate (0.06 g), propylene carbonate (3 ml) and the prepared redox chromophore (0.06 g). All ingredients are mixed thoroughly after mixing together using a speed mixer.
  • the paste-like formulation obtained is applied according to the prior art in the case of a display between intersecting electrodes. When a voltage is applied, a color change from blue to colorless (white) is achieved.
  • the prior art formulation is improved in that the redox system becomes part of the electroactive chromophore. Since here for the first time the organic chromophore contains the redox system itself, can be dispensed with the addition of redox system based on quinone / hydroquinone. This can reduce the number of components in the formulation. It is of particular advantage that the elimination of the chlorine / hydroquinone system improves the long-term stability of the electrodes compared to the now neutral formulation. Furthermore, an improved stability of the formulation and thus an improved life of the display is achieved.
  • the advantage of the redox chromophores according to the invention is, inter alia, that a large variety of structural changes is available in the coloring part of the molecule, as a result of which a large selection of very different colors can be represented.

Landscapes

  • Physics & Mathematics (AREA)
  • Nonlinear Science (AREA)
  • Chemical & Material Sciences (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Electrochromic Elements, Electrophoresis, Or Variable Reflection Or Absorption Elements (AREA)

Abstract

L'invention concerne un matériau destiné à des couches électrochromes à base d'un virage de couleur provoqué par une réaction d'oxydoréduction. Selon l'invention, les fonctions du système d'oxydoréduction et du chromophore électroactif sont réunies dans un composant. La réunion des fonctions permet de s'affranchir d'au moins un composant dans des formulations électrochromes.
PCT/EP2006/062538 2005-05-31 2006-05-23 Materiau destine a des couches electrochromes Ceased WO2006128809A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DE102005024961 2005-05-31
DE102005024961.2 2005-05-31
DE102005031635.2 2005-07-06
DE102005031635 2005-07-06

Publications (1)

Publication Number Publication Date
WO2006128809A1 true WO2006128809A1 (fr) 2006-12-07

Family

ID=36754670

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2006/062538 Ceased WO2006128809A1 (fr) 2005-05-31 2006-05-23 Materiau destine a des couches electrochromes

Country Status (1)

Country Link
WO (1) WO2006128809A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008077863A1 (fr) * 2006-12-21 2008-07-03 Siemens Aktiengesellschaft Dérivés de pyridinium à réaction cathodique pour formulation électrochrome

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2534713A1 (de) * 1975-08-04 1977-02-17 Dirk Dr Basting Farbstofflaser
WO1996007487A1 (fr) * 1994-09-10 1996-03-14 The University Of Liverpool Procede de synthese de materiaux aux proprietes electroniques, magnetiques et/ou optiques regulees
WO2001027690A2 (fr) * 1999-10-11 2001-04-19 University College Dublin Dispositif electrochromique
WO2002075441A2 (fr) * 2001-03-19 2002-09-26 Dow Global Technologies Inc. Dispositif d'affichage electrochromique et compositions utilisees pour fabriquer de tels dispositifs
WO2006056550A1 (fr) * 2004-11-24 2006-06-01 Siemens Aktiengesellschaft Composant electrochrome comportant un hydrogel rempli d'electrolyte

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2534713A1 (de) * 1975-08-04 1977-02-17 Dirk Dr Basting Farbstofflaser
WO1996007487A1 (fr) * 1994-09-10 1996-03-14 The University Of Liverpool Procede de synthese de materiaux aux proprietes electroniques, magnetiques et/ou optiques regulees
WO2001027690A2 (fr) * 1999-10-11 2001-04-19 University College Dublin Dispositif electrochromique
WO2002075441A2 (fr) * 2001-03-19 2002-09-26 Dow Global Technologies Inc. Dispositif d'affichage electrochromique et compositions utilisees pour fabriquer de tels dispositifs
WO2006056550A1 (fr) * 2004-11-24 2006-06-01 Siemens Aktiengesellschaft Composant electrochrome comportant un hydrogel rempli d'electrolyte

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008077863A1 (fr) * 2006-12-21 2008-07-03 Siemens Aktiengesellschaft Dérivés de pyridinium à réaction cathodique pour formulation électrochrome

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